Catalytic construction and reconstruction of guanidines: Ti-mediated guanylation of amines and transamination of guanidines

Tiow-Gan Ong; Glenn P A Yap; Darrin S Richeson

doi:10.1021/ja035716j

Catalytic construction and reconstruction of guanidines: Ti-mediated guanylation of amines and transamination of guanidines

J Am Chem Soc. 2003 Jul 9;125(27):8100-1. doi: 10.1021/ja035716j.

Authors

Tiow-Gan Ong¹, Glenn P A Yap, Darrin S Richeson

Affiliation

¹ Department of Chemistry, Center for Catalysis Research and Innovation, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.

PMID: 12837069
DOI: 10.1021/ja035716j

Abstract

Bis(guanidinate) titanium imido complexes [{(Me2N)C(NiPr)2}2TiNAr'] (Ar' = 2,6-Me2C6H3 (1a); C6F5 (1b)) are competent catalysts for the guanylation of a variety of arylamines with carbodiimide. The reversible [2 + 2] addition of iPrN=C=NiPr to 1b is demonstrated and is proposed to be part of the catalytic cycle. Compounds 1a and 1b are also effective precatalysts for the transamination of trialkylguanidines with arylamines to yield aryldialkylguanidines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry*
Catalysis
Guanidines / chemical synthesis
Guanidines / chemistry*
Organometallic Compounds / chemistry
Titanium / chemistry

Substances

Amines
Guanidines
Organometallic Compounds
Titanium